Shortening emulsifiers and method of using same



:amount of emulsifier added to the icing is based United States PatentSHORTENIN G EMULSIFIERS AND METHOD OF USING SAME Stephen S. Chang, ParkForest, Forrest L. De Vere, Bloomington, and Marvin A. Friedman, ParkForest, 111., assignors to Swift & Company, Chicago, 111., a corporationof Illinois No Drawing. Filed Dec. 3, 1957, Ser. No. 700,291 14 Claims.(Cl. 99-118) The present invention relates to improved agents for icingshortenings. More particularly, the subject invention is directed todiglycerides of certain fatty and hydroxy acids and their use asemulsifiers in icing shortenings.

Several years ago it was discovered that so-called super glycerinateds-hortenings containing monoglycerides and diglycerides and texture.More recently,-it has been found that even better cakes result whendiglyceride materials prepared from glycerine, higher fatty acids, andlower by .droxy acids are used as shortening agents. Compounds producedcakes of superior grain rofthis type are described in the United Statespatent to Iveson et al., No. 2,690,971, wherein the lower hydroxy acidsare described as organic mono-hydroxy carboxylic acids of not over sixcarbon atoms having the general formula RCHOHCOOH wherein R representshydrogen or a hydrocarbon bon atoms. e

. "Inaddition to their use in cakes, Iargequantities of emulsifiers orshortening agents are consumed in making icings for various pastryproducts. Icings usually "consist of fat, powdered sugar, salt, milk,and flavoring and have considerable amounts of air beaten into the fat.Those icing materials which are placed between layers of a cake or areincorporated within a pastry product, 'are often designated as creamfillers. Generally, a

group having one to four cari cream filler icing contains more fat andmore water than an icing which 'is used as a coating for pastries. Thefollowing formulas are typical of a cream filler icing and a coatingicing:

The particular ingredients used, as well as the percentage of eachmaterial, depend on individual preference and .the type of cake.formula,

or pastry being prepared. In the above fat includes the shorteningagent. The

on a certain percentage of oil present in the product.

- Although super glycerinated emulsifiers and emulsifiers of the Ivesonet al. type have been added to icings to-increase their volume andproduce a smoother prodnot, they have not proven to be entirelysatisfactory for these purposes.

Itis an object of the present invention, therefore, to prepare newshortening agents which will improve the ,appearance and volume of cakeicings.

Another object of the present invention is to provide 'a'method ofpreparing new and improved icing shortenings.

:anmsmlev- 2,966,410 Patented Dec. 27, 1969 mono-fatty acid esters, thatthese materials will produce texture of the product. p V The followingexamples are illustrative of the present invention:

superior icing volumes and improve, the. appearance and Example 1 Onemole of myristic acid, one mole of lactic acid, and one mole of glycerinwere mixed in a vessel fitted with a stirrer and a reflux condenser andwere heated to 185 C. The reactants were kept at this temperature for 6/2 hours, during which time the material was constantly agitated. Acurrent of carbon dioxide was bubbled through the molten materials forthe first 5 hours of the reaction. A vacuum of 15-21 inches was appliedto the vessel during the last 2. hours of thisjS hour. period. A 1 mm.vacuum was then applied and the product was steam stripped at 185 C. for1 /2 hours.

The addition of up to 10% of the product prepared as shown above to ahydrogenated vegetable fat gave the following results when thefat wasincorporated in a cream filler icing;

Percent t Specific M Emulsifier Gravity H -OM IOIWO Examp l ell In thefollowing table, Emulsifier A was prepared in accordance with the'Iveson, et al., teaching, using palmitic -acid and 20% myristic acid asthe fatty acid component, and Emulsifier B was prepared as described inExample I:

Specific Emulsifier Gravity of Cream Filler Icing 5% Monoglycerides 0.700 5% Mon0glycerides5% Emulsifier A.-. 0. 715 5% Monoglycerides+10%Emulsifier A. 0. 730 5% Monoglycerldes20% Emulsifier A 0. 740 5%Monoglycerides-5% Emulsifier ]3 0.550 5% Monoglycerldes-l-l0% EmulsifierB. 0. 490

It is apparent'from the data given in Examples I and II that the use ofmyristic acid as the predominant fatty acid component of the emulsifierlowers the specific gravity of the icing and correspondingly increasesthe icing volume.

Example 111 A series of emulsifiers was prepared as described in ExampleI from glycerin, lactic acid, and from various proportions of myristicand palmitic acids. The follow- 3 ing table sets forth a comparison ofthe effectiveness-of these materials.

130 0090, t i0 1w-- pe ific Myr stic Palmiticerides Gravity Acid Acid ofIcing 100 0 2 /4 0.440 .9 1. :2 /z 9.450 80 20 2% 0. 460 70 30 are 10.475 00 :40 2 /2 0. 485

aram ilalv in a sin'iila'i' comparative test, a group of emulsifierswasprepared as described in Example I from glycerin, lactic acid andfrom various proportions of myristic and stearic acids. The results ofthe test were as follows:

Perceritpf Percent of Monogly- Specific Myr st-rc Stearic ceridesGravity Acid Acid of Icing 00 10 2V. 0. 485 so 20 2% 0. 525 00 to 2%0.535 50 50 25 2 0. s00

The tablesin Examples III and IV again demonstrate that shorteningagents containing less than 60% myristic acid are markedly inferior tothe emulsifiers of the present invention.

Example 'V "The results in a test showing the comparativevalue othersewd. oao li q des. of ,(l), "yt t c t palmitic acid and (-3) stearicacid as icing emulsifiers are set forth below. The additives were usedat a 4% level based on the weight of the oil in the icing. 4o

Acid Usedin Monogly- Specific Bose Oil Emulsifier cerides, Gravitypercent of Icing 'AnimalFat; Myristicufl 0.730 '-Dn-' 1* 1 1.0% Do... Sar 1.095 DO -..L' 2% 1.020

Exiz'mple VI The following table shows the eifectiveness of variousamounts of an emulsifier prepared as described in Example I when used inan icing shortening:

Amount Specific Base Oil of Emul- Gravity sifier, of Icing percentvegetable Oil Shortening I 0 0. 030 Do a 3 0.015 Do 7 v a 5 0.590 Do I 00. 565 Do. 7 0. 040 Do 8 0. 525 Do-.. 10 0400 Animal Oi Shorten g +3%Monoglycerides 0 0,015 D 5 0.565 Animal and Vegetable Oil Shortening +5%Mono- 5 glgperidesfln; 0 0.035 6 Although our preferred product isprepared from equal molar amounts of fatty acid, hydroxy acid, andglycerin, it is possible tOLUSQ IDOI'e QI less than one mole of hy'droxy acid and still produce an acceptable although somewhat inferioremulsifier. Similarly, more "or less than one 'mole {if glycerin and/6rfatty acid could be pound of diglyceride. "containi'ng from about 60% tomyristic acid show a 4 used although this again would produce a somewhatinferior product.

When a one-to-one-to-one mole ratio is used, we obtain about 10%triglyceride material, 15% monoglyceride material, and 75% diglyceridematerial. The diglyceride portion is composed mainly of lactomyristateWhere lactic acid and myristic acid are employed, although somedimyristin would also be formed.

The subject icing shortening additives could be prepared at temperatureslower than the usual 185 C. although this would require longer reactiontimes. We have conducted tests, for example, wherein the product wasmade at C. as well as C. At the higher temperature the reaction was rununder a'CO protective blanket for 3 hours and then under a vacuum for 2additional hours. At 170 C. the reaction required 4 hours under the COblanket followed by 3 hours under the vacuum.

In our preferred embodiment the reaction is conducted in a closedvessel. Carbon dioxide or another inert gas is passed continuouslythrough the mixture to (I) carry out H 0, (2) to prevent oxidativedeterioration, and (3) to inhibit discoloration. Following thecompletion of the reaction, the product is steam stripped to remove allmaterials having a vapor pressure higher than the desired lactic acid asthe hydroxy acid, other similar materials "such as hydroxy butyric acid,hydroii'y valeric acid, etc., "could also be employed in preparing theproduct.

As was indicated in the examples, the preferred comthe present inventioncontains at least about 80% inyristic acid as the fatty acid componentof the It has been found, however, that materials significantimprovement over other shortening agents when used as additives in icing'shortenings. If desired, these materials can be used along withmonoglycerides or other emulsifiers. It is desirable in most cases toadd to'the shorteningabout 1% to about 10% based on the weight of'theshortening of the reaction product.

Obviously, many modifications and variations of the invention ashereinbefore set forth may be made without departing from the spirit andscope thereof, and therefore only such limitations should be imposed 'asare indicated in the appended claims.

We claim:

1. An improved shortening for use in icings which comprises: ashortening selected from the group consisting of vegetable fats, meatfats, and mixtures thereof and at least about 1.0% of the diglyceridereaction products of glycerimhigher fatty acids at least 60% by weightof which is myristic acid, and an alkyl monohy'droxy monocarboxylic acidof from 2 to 6 carbon atoms, at least about 50% of said diglyceridereaction products having a monohydroxy, monocarboxylic acid radical offrom 2 too carbon atoms and a higher fatty acid radical.

2. improved shortening for use in icings which comprises: ashorteningselected from the group consisting of vegetable fats, meat fats, andmixtures thereof'and at least about. 110% of tlre diglyceridereac'tionproducts of lmolar equivalent of glycerin, 1 molar equivalent of higherfatty acids at'least 60% by weight or which is myristic acid, and 1molar equivalent of an alkyl monohydroxyjmonocarboxylic acid of from 2to 6 carbon I 4. An ,improve'd 'sho'rtening for use inicings'asin'claiha wherein the "rnonohydroxy carbonylic acid is lacticacid.

5. An improved shortening agent for use in icings which comprises: thereaction products of glycerin, higher fatty acids at least 60% by weightof which is myristic acid, and an alkyl monohydroxy monocarboxylic acidof from 2 to 6 carbon atoms, at least about 50% of said reactionproducts having a monohydroxy, monocarboxylic acid radical of from 2 to6 carbon atoms and a higher fatty acid radical.

6. An improved shortening agent for use in icings which comprises: thereaction products of 1 molar equivalent of glycerin, 1 molar equivalentof higher fatty acids at least 60% by weight of which is myristic acid,and 1 molar equivalent of an alkyl monohydroxy monocarboxylic acid offrom 2 to 6 carbon atoms.

7. An improved shortening agent for use in icings as in claim 5 whereinthe monohydroxy monocarboxylic acid of from 2 to 6 carbon atoms islactic acid.

8. An improved shortening agent for use in icings as in claim 6 whereinthe monohydroxy carboxylic acid is lactic acid.

9. A method of improving the shortening qualities of a shorteningselected from the group consisting of vegetable fats, meat fats, andmixtures thereof which comprises: adding to said shortening a minoramount of the diglyceride reaction products of glycerin, higher fattyacids at least 60% by weight of which is myristic acid, and an alkylmonohydroxy monocarboxylic acid of from 2 to 6 carbon atoms, at leastabout 50% of said diglyceride reaction products having a monohydroxy,monocarboxylic acid radical of from 2 to 6 carbon atoms and a higherfatty acid radical.

10. A method of improving the shortening qualities of a shorteningselected from the group consisting of vegetable fats, meat fats, andmixtures thereof which comprises: adding to said shortening a minoramount of the reaction products of 1 molar equivalent of glycerin, 1molar equivalent of higher fatty acids at least 60% by weight of whichis myristic acid, and 1 molar equivalent of an alkyl monohydroxymonocarboxylic acid of from 2 to 6 carbon atoms.

11. A method of improving the shortening qualities of a shorteningselected from the group consisting of vegetable fats, meat fats, andmixtures thereof which comprises: adding to said shortening from about 1to about 10% by weight of the diglyceride reaction products of glycerin,higher fatty acids at least 60% by weight of which is myristic acid, andan alkyl monohydroxy monocarboxylic acid from 2 to 6 carbon atoms, atleast about of said digylceride reaction products having a monohydroxy,monocarboxylic acid radical of from 2 to 6 carbon atoms and a higherfatty acid radical.

12. A method as in claim 9 wherein the monohydroxy monocarboxylic acidis lactic acid.

13. A method as in claim 10 wherein the monohydroXy monocarboxylic acidis lactic acid.

14. A method as in claim 11 wherein the monohydroxy monocarboxylic acidis lactic acid.

References Cited in the file of this patent UNITED STATES PATENTS2,480,332 Little Aug. 30, 1949

1. AN IMPROVED SHORTENING FOR USE IN ICINGS WHICH COMPRISES: ASHORTENING SELECTED FROM THE GROUP CONSISTING OF VEGETABLE FATS, MEATSFATS, AND MIXTURES THEREOF AND AT LEAST ABOUT 1.0% OF THE DIGLYCERIDEREACTION PRODUCTS OF GLYCERIN, HIGHER FATTY ACIDS AT LEAST 60% BY WEIGHTOF WHICH IS MYRISTIC ACID, AND AN ALKYL MONOHYDROXY MONOCARBOXYLIC ACIDOF FROM 2 TO 6 CARBON ATOMS, AT LEAST ABOUT 50% OF SAID DIGLYCERIDEREACTION PRODUCTS HAVING A MONOHYDROXY, MONOCARBOXYLIC ACID RADICAL OFFROM 2 TO 6 CARBON ATOMS AND A HIGHER FATTY ACID RADICAL.